1. Synthesis of Pimprinine and Oxaprozin from Enamides
Work Presentation
Synthesis of Pimprinine and Oxaprozin
from Enamides
Yunhui Zheng 1

2. Pimprinine 2

3. ̶ 11 entry oxidant additive (equiv) solvent temp(OC) yield(%) 1 PIDA
BF3.Et2O (2.0)
DCE
reflux
decomposed 2
DCM
-78 3
BF3.Et2O (0.1) 4 ̶ NR 5 6 rt 7 ND 8
AgCO3(2.0) 9
ACN 10
1,4-dioxane 11
TFE 3

4. 4

5. 5

6. Oxaprozin
It is a non-steroidal anti-inflammatory drug, used to relieve the inflammation, swelling, stiffness, and joint pain associated with osteoarthritis and rheumatoid arthritis.
Previous work
This work 6

7. Route A 7

8. Route B 8

9. 9

10. Thank you!